ESSENCE Network: Karleen Roy Shares How She Went From Diddy's Assistant to Her Own Boss

Michael Rowe

Ever wondered who celebrities call when they want to swim with sharks or need a Birkin bag tomorrow that’s only sold in Paris? The phone that rings belongs to Karleen Roy. Roy learned the entertainment industry firsthand as Sean “Diddy” Combs' executive assistant for six years. Now she shares her journey and secrets to becoming a boss.

Ever wondered who celebrities call when they want to swim with sharks or need a Birkin bag tomorrow that’s only sold in Paris? The phone that rings belongs to Karleen Roy. Roy learned the entertainment industry firsthand as Sean “Diddy” Combs' executive assistant for six years. Now she shares her journey and secrets to becoming a boss.

The gig: I’m the founder of The Vanity Group, a boutique luxury lifestyle management company specializing in event production, luxury concierge services and talent relations for the biggest names of our time. Some of our clients include Sean "Diddy" Combs, Kobe Bryant, and Maybach Music Group. The job ranges from red carpet events all over the world, organizing once-in-a-lifetime holidays, to connecting major brands to top talent. It's a wild job for the most exigent of clients.

The journey: When I was in Memphis I thought I was going to be a dermatologist or something to do with beauty. When I got to Howard University, my plans to be a doctor went out the window quickly. One day I was watching Sex and the City and realized I wanted to Samantha’s job. I worked in PR for a few years then interviewed to be Sean Comb’s assistant. I worked for Bad Boy for six years then realized I was ready for my next chapter. I took some time off, and colleagues I knew began to hire me for a variety of projects such as securing talent for red carpet events, planning events and assisting clients with over-the-top requests. Then the light bulb went off: “This is a business!”

Her business highlight: I got a call from the assistant for rapper Fabulous last year. He wanted to hire me to plan his birthday party. It was Wednesday and the party was for Monday. He wanted a big party with the Great Gatsby theme. The moment I hung up the phone I started brainstorming and calling all my vendors with all of our ideas. We sent out invites on Friday. We had luxury cars, an amazing venue, a live band and built a custom stage. It was a huge success for Great Fabsy. At that moment, I knew that this was what I was supposed to be doing.

Success 101: What has worked for me is maintaining my excellent relationships. I don’t think I’d be where I am if I didn’t have those great people backing me and championing me, and helping me get clients.

Her biggest lesson learned: Not going with my gut. Trust your gut. Every time I’ve gone against my gut, it’s come back to bite me in the butt.

Her hustling tip: Do not treat your business like it’s a side hustle. Take it very seriously. When you treat your business like it’s something you do on the side, other people will as well. If you take your business seriously, people will respond appropriately. I would also tell young people to master your craft, before you start your own business.

Her best time-saving tip: You have to write everything down. When the going gets tough, there’s no way in the world you’re going to remember everything you need to do. I also respond to emails as soon as I get them. I treat everything like a 911 emergency. I don’t care if it’s getting my hair done or my mom needs Tylenol or a client needs a boat.

In her downtime: I walk in the park every evening.That’s my downtime. I try not to answer any emails during that time. I read a lot. I just read Lean In by Sheryl Sandberg and I just bought Girl Boss by Sophia Amoruso.

Her tech fix: My favorite apps are Turbo Scan for documents. And I just discovered Instasize.

In her beauty bag: I’m obsessed with Iman’s BB cream. That’s my number one go-to. I’m always hot so I use MAC Engraved; it’s the best eyeliner I have ever got and it stays in my bag. I’m also obsessed with scents. Lately I’ve been wearing Carolina Herrera 212 Sexy. My new thing I’m trying to embrace is lip colors.

Her go-to power accessory: I love fashion and feel most powerful wearing skirts. I also love old jewelry!

Her theme song: “It Ain’t Over” by Maurette Brown Clark I’m so blessed and there are still so many more great things to come. It reminds me to not remain complacent.